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United States
Massachusetts

Dukes County

The best cycling routes in Dukes County

4.8

(95)

1,553

riders

62

rides

Touring cycling in Dukes County offers diverse landscapes, from extensive oceanfront vistas and golden beaches to serene inland forests and farmlands. The region is characterized by predominantly flat to gently rolling terrain, with some routes featuring more challenging hilly sections. Martha's Vineyard, a key part of the county, provides over 44 miles of dedicated paved bike paths connecting major towns and attractions. Cyclists can explore coastal areas, dense woodlands, and open landscapes, often encountering tranquil ponds and historic landmarks.

Best…

Last updated: June 29, 2026

4.9

(8)

126

riders

#1.

Joseph Sylvia State Beach – Historic Edgartown loop from Edgartown

15.8km

00:53

30m

30m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Popular around Dukes County

Cycling around Edgartown

Cycling around Vineyard Haven

Cycling in Manuel F. Correllus State Forest

Cycling in South Beach State Park

Cycling around Oak Bluffs

Hiking in Dukes County

Road Cycling Routes in Dukes County

Running Trails in Dukes County

Tips from the Community

Jan
June 22, 2025, Menemsha Bike Ferry

Ferry runs Sat/Sun 9-5 on request

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Zachary
September 19, 2024, East Chop Lighthouse

This historic lighthouse was built in 1878 and is maintained by the Martha's Vineyard Museum. The museum runs $5 sunset tours during the summer, and the lighthouse is also available to be rented out as a venue for weddings and other events.

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Ulrike
August 19, 2024, Harts Harbor

The cycle paths are well developed and there is little traffic.

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A very beautiful beach with white sand and clear water.

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A beautiful spot and a great starting point for bike tours. There are plenty of rental companies there. E-bikes are quite expensive though, ~$75 per day.

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Moshup Beach, also known as Aquinnah Public Beach, borders Gay Head Beach, which lies below the cliffs. https://www.savebuzzardsbay.org/places-to-go/moshup-beach/ In August 1991, Hurricane Bob altered much of Martha's Vineyard's coastline. Moshup Beach now has clay cliffs as well. Before the storm, there were only sand dunes here. https://vineyardgazette.com/news/1991/08/30/changing-island-face-storms-surgical-srike

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Matthew
February 19, 2024, Harts Harbor

Sandwiched between Joseph Sylvia State Beach and the Felix Neck Conservation Area, Harts Harbor is a large body of water. It's actually an extension of Sengekontacket Pond and is nice to look at as you ride along the bike path.

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Amy
February 19, 2024, Joseph Sylvia State Beach

With soft, golden sand and shallow water, Joseph Sylvia State Beach is a popular hangout spot on Martha's Vineyard. The beach extends 5 miles (8 km) between Oak Bluffs and Edgartown. It's public and not privately owned like many of the island's beaches. On one side, the Atlantic Ocean glistens into the horizon and on the other, Cow Bay stretches around the coast. It's popular for windsurfing and kitesurfing when the weather is right.

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Frequently Asked Questions

How many touring cycling routes are available in Dukes County?

Dukes County offers a wide selection of touring cycling routes, with over 50 options available on komoot. These routes cater to various preferences, from leisurely coastal rides to more challenging inland explorations.

What is the best time of year for touring cycling in Dukes County?

The prime seasons for touring cycling in Dukes County are summer and early fall. Warm summer days are often cooled by ocean breezes, while early fall brings pleasant temperatures, quieter roads, and spectacular foliage, making it an ideal time to explore the island's diverse landscapes.

What kind of terrain can I expect on Dukes County cycling routes?

The terrain in Dukes County is predominantly flat to gently rolling, making it suitable for leisurely rides. However, some routes do feature more challenging hilly sections for experienced cyclists. You'll find extensive paved bike paths, quiet forested trails, and routes traversing farmlands and open landscapes.

Are there easy touring cycling routes suitable for beginners or families?

Yes, Dukes County is very family-friendly, with over 35 easy touring cycling routes. The island features over 44 miles of dedicated, well-maintained paved bike paths, ensuring safe and accessible cycling for all skill levels. An excellent option is the Joseph Sylvia State Beach – Historic Edgartown loop from Edgartown, an easy 11-mile route connecting a popular state beach with the historic town.

Are there any challenging touring cycling routes for experienced riders?

While much of Dukes County is flat, there are routes that offer more challenge. For instance, the Vineyard Haven Harbor – Seth's Pond loop from Oak Bluffs is a difficult 50-mile route with significant elevation gain, providing a more strenuous experience for seasoned cyclists.

What scenic viewpoints or natural attractions can I see along the touring cycling routes?

Dukes County's routes offer stunning natural beauty. You can cycle past the dramatic clay cliffs of Aquinnah, enjoy oceanfront vistas at Joseph Sylvia State Beach, or explore the serene inland areas of the Manuel F. Correllus State Forest. The Long Point Wildlife Refuge also offers a rich blend of coastal beauty and thriving ecosystems.

Are there any circular touring cycling routes in Dukes County?

Many touring cycling routes in Dukes County are designed as loops, allowing you to start and end in the same location. Examples include the Historic Edgartown – Joseph Sylvia State Beach loop from Oak Bluffs, which features scenic coastal stretches, and the Aquinnah Headlands Preserve – Menemsha loop from Tipson Pond Lot, leading through dramatic clay cliffs.

What do other touring cyclists enjoy the most about touring cycling in Dukes County?

The area is highly rated by the komoot community, with an average score of 4.8 stars from over 40 reviews. Reviewers often praise the diverse landscapes, from captivating oceanfront vistas and golden beaches to serene inland forests and farmlands, as well as the extensive network of well-maintained bike paths.

Are there opportunities to explore charming towns or historic landmarks by bike?

Absolutely. Cycling routes frequently pass through or link charming towns such as Historic Edgartown, Oak Bluffs, and Vineyard Haven. This allows riders to easily visit shops, galleries, and historic landmarks like Oak Bluffs' distinctive gingerbread cottages. The Harts Harbor – Historic Edgartown loop from Edgartown is a great option for combining natural beauty with town exploration.

Is public transport available to access bike paths in Dukes County?

Martha's Vineyard has a public bus system that connects major towns and can be used to access various points along the island's extensive bike path network. This offers flexibility for cyclists who may not want to ride the entire distance or wish to start their tour from a specific location.

Can I find bike rentals, including e-bikes, in Dukes County?

Yes, for those without their own bicycles, rental options, including e-bikes, are readily available across Martha's Vineyard. This makes it convenient for visitors to enjoy the island's cycling opportunities without bringing their own equipment.

Are there any unique experiences for cyclists in Dukes County?

A unique highlight for cyclists in Dukes County is the Menemsha Bike Ferry, which provides an interesting detour and connects different parts of the island, offering a memorable experience as part of your ride.

What are some of the longer touring cycling routes available?

For those looking for longer rides, routes like the Historic Edgartown – Joseph Sylvia State Beach loop from Vineyard Haven cover over 25 miles, offering an extended exploration of the island's coastal and inland beauty. This route is classified as moderate, providing a good balance of distance and accessibility.

Most popular routes in Dukes County

Hiking in Dukes County

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Check out more Cycling routes throughout Dukes County below and find the perfect route in your destination.

Manuel F. Correllus State ForestOak BluffsEdgartownVineyard HavenSouth Beach State Park

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Things to Do in Manuel F. Correllus State Forest

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